CN105817263B - A kind of vinyl ferrocene oligomer catalyst being catalyzed ammonium perchlorate decomposition - Google Patents
A kind of vinyl ferrocene oligomer catalyst being catalyzed ammonium perchlorate decomposition Download PDFInfo
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- CN105817263B CN105817263B CN201610223569.3A CN201610223569A CN105817263B CN 105817263 B CN105817263 B CN 105817263B CN 201610223569 A CN201610223569 A CN 201610223569A CN 105817263 B CN105817263 B CN 105817263B
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
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- C06—EXPLOSIVES; MATCHES
- C06D—MEANS FOR GENERATING SMOKE OR MIST; GAS-ATTACK COMPOSITIONS; GENERATION OF GAS FOR BLASTING OR PROPULSION (CHEMICAL PART)
- C06D5/00—Generation of pressure gas, e.g. for blasting cartridges, starting cartridges, rockets
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- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
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Abstract
The invention discloses a kind of for being catalyzed the vinyl ferrocene oligomer catalyst of ammonium perchlorate decomposition.The present invention is using vinyl ferrocene as polymerized monomer, high Fe content (24.3~26.3%) have been synthesized by anionic polymerisation, vinyl ferrocene oligomer catalyst of the molecular weight in 400~5000 ranges, and be applied in the catalytic decomposition of ammonium perchlorate.The catalyst is not volatile, there is significant catalytic effect to the thermal decomposition of ammonium perchlorate, there is extremely low impact sensitivity (10%~14%) with ammonium perchlorate two end number mixing objects system, far below the high sensitivity of the pungent corresponding system 98% of Kato generally used, it can be used as the catalyst of catalysis ammonium perchlorate decomposition, and be applied in many kinds of solids propellant and gas generator propellant using ammonium perchlorate as oxidant.
Description
Technical field
The invention discloses a kind of vinyl ferrocene oligomer catalyst, and in particular to one kind is for being catalyzed ammonium perchlorate
The vinyl ferrocene oligomer catalyst of decomposition.
Background technique
Ferrocene analog derivative is a kind of important metallo-organic compound.Ferrocene and its derivative can be catalyzed high chlorine
Pyrolytic exothermic temperature and the fuming-off temperature decline of ammonium perchlorate, therefore ferrocene and its derivative are realized in the thermal decomposition of sour ammonium
Object is a kind of good positive burningrate catalyst.Ferrocene derivatives are widely used to using ammonium perchlorate as oxidant at present
In many kinds of solids propellant and gas generator propellant.Kubota(Kubota,N.Propellants and Explosives:
Thermochemical Aspects of Combustion,2nd,Completely Revised and Extended
Edition；John Wiley&Sons Ltd., 2007) iron content is higher in the ferrocene class catalyst illustrated, to perchloric acid
The catalytic decomposition efficiency of ammonium is higher, and corresponding propellant burning rate is higher, this has also been the common recognition of domestic and international researcher.
The report of ferrocene class catalyst is more in document and patent, but mostly alkyl monokaryon ferrocene and alkyl double-core two
Luxuriant iron derivative.Wherein monokaryon ferrocene derivatives iron content partially has been used for the burn rate of certain propellants up to 20%-26%
Catalyst, but its generally existing volatile problem, limit its large-scale application.In addition, monokaryon ferrocene derivatives and double
Core ferrocene problem high there is also mechanical sensitivity after being mixed with ammonium perchlorate, and restrict a key factor of its application.
The Butacene that state-run explosive wastewater company, France reports a kind of end hydroxy butadiene adhesive glue side chain graft ferrocene is urged
Agent is divided into " Butacene-7 " (Fe content about 7%) and " Butacene-3 " (Fe content is about 3%) by iron content difference,
It can effectively be catalyzed the decomposition of ammonium perchlorate in solid propellant, but since synthesis process is complex, increase its cost, and
Its iron content is again very low, therefore does not obtain large-scale application at home.Vinyl ferrocene is also a kind of two cyclopentadienyl of small molecule monokaryon
Iron, iron content are up to 26.4%, but its directly use is similar to other small molecule ferrocene catalyst, volatilization migration is obvious.
It is no lack of the polymerization report of ferrocene class compound, including free radical polymerization, cationic polymerization, polycondensation in Polymer Synthesizing document
With hot open loop, but the degree of polymerization is all very high, is not yet seen from presently disclosed document with vinyl ferrocene or derivatives thereof work
The report used for ammonium perchlorate decomposition catalyst.(Nuyken, the O. such as Nuyken in 1997；Burkhardt,V.；Hubsch,
C.Macromol.Chem.Phys.1997,198,3353) the controllable anionic polymerisation of vinyl ferrocene is reported, but have no
The report of polymer application.
The present invention using vinyl ferrocene as polymerized monomer, by anionic polymerisation synthesized high Fe content (20.6%~
26.3%), in 400~5000 ranges, the vinyl ferrocene oligomer for being catalyzed ammonium perchlorate decomposition is catalyzed molecular weight
Agent.The catalyst is not volatile, can preferably be catalyzed the decomposition of ammonium perchlorate, has pole with ammonium perchlorate two end number mixing objects system
Low impact sensitivity (10%~14%) is significantly less than the high sensitivity (98%) of the corresponding system of the Kato generally used pungent (GFP)
(the energetic material such as Zhang Wei, Yang Jun, Yu Yan, 2011,19,627).
Summary of the invention
The object of the present invention is to provide a kind of for being catalyzed the vinyl ferrocene oligomer catalyst of ammonium perchlorate decomposition,
Preparation method and application, and be successfully applied in the catalytic decomposition of ammonium perchlorate.Using vinyl ferrocene as polymerized monomer,
It can be with the vinyl ferrocene oligomer of the different molecular weight of synthesized high iron content by anionic polymerisation.
The present invention overcomes the volatile disadvantages of small molecule ferrocene class catalyst, greatly reduce the catalysis of ferrocene class
Agent/ammonium perchlorate binary mixture impact sensitivity, and solve that aggretion type side chain graft ferrocene catalyst iron content is low to ask
Topic.The catalyst molecule amount of synthesis is controllable, has significant catalytic decomposition effect to ammonium perchlorate, and not volatile, iron content is high,
It is low with the sensitivity of ammonium perchlorate binary mixture.
The structural formula of vinyl ferrocene oligomer catalyst of the present invention are as follows:
Wherein R is normal-butyl or sec-butyl, and iron content is 20.6%~26.3%, and molecular weight is 400~5000, n=1~24,
Preferential selection n=2~24.
The synthetic method of vinyl ferrocene oligomer catalyst of the present invention, be under the conditions of anhydrous and oxygen-free, in-
At 20~-10 DEG C, tetramethylethylenediamine (TMEDA) and butyl lithium solution reaction 1 are added into the THF solution of vinyl ferrocene
~8h adds anhydrous methanol and is quenched, be added organic solvent be precipitated precipitating, filter, washing, then use organic dissolution, filter, filtrate
Vacuum distillation removes solvent, obtains vinyl ferrocene oligomer product；The initiator butyl lithium and vinyl ferrocene list
The molar ratio of body is 1:2~30.
Organic solvent of the present invention for precipitating to be precipitated is that methanol, ethyl alcohol, isopropanol or their mixing are organic
Solvent.
Organic solvent of the present invention for dissolving filter cake is methylene chloride, ethyl acetate, chloroform, bis- chloroethene of 1,2-
Alkane or their mixed organic solvents.
The vinyl ferrocene oligomer for the high Fe content that the present invention obtains vinyl ferrocene anionic polymerisation is catalyzed
Agent is applied to the catalytic decomposition of ammonium perchlorate.Compared with prior art, the present invention has the advantage that the catalyst molecule amount can
It adjusts, not volatile, iron content is high, and the catalyst is low with the impact sensitivity for the binary mixture that ammonium perchlorate forms, stability
Well.Vinyl ferrocene oligomer/thin and tall ammonium chlorate (D50=45 μm) binary mixture impact sensitivity be 10~14%.
Detailed description of the invention
Thermogravimetric (TG) curve of Fig. 1 vinyl ferrocene oligomer
The pure thin and tall ammonium chlorate (D of Fig. 250=45 μm) differential scanning calorimetric analysis (DSC) curve
Fig. 3 vinyl ferrocene oligomer/thin and tall ammonium chlorate (D50=45 μm) (mass fraction 5:95) binary mixture
Differential scanning calorimetric analysis (DSC) curve
Wherein weight is weight fraction, and Temperature is temperature, and Heat Flow is hot-fluid, and Exo Up is to put upwards
Heat, Temperature are temperature.
Specific embodiment
It will further facilitate the understanding present invention by following embodiments, but the contents of the present invention can not be limited.
The synthesis of vinyl ferrocene oligomer
[embodiment 1]
Under the conditions of anhydrous and oxygen-free, vinylferrocene monomer (5.30g, 25mmol) is added in Schlenk bottles of 100mL,
Anhydrous THF (20mL), TMEDA (0.45mL, 3mmol).Reaction solution is refrigerated to -20 to -10 DEG C, and it is molten that initiator n-BuLi is added
Liquid (0.33mL, 2.5M, 0.83mmol), reaction solution become blood red, and after reacting 8h, anhydrous methanol is added into reaction system
(1mL) terminates reaction.Anhydrous methanol (60mL) is added, precipitating is precipitated, filters, wash filter residue, filter residue methylene chloride with methanol
Dissolution, is obtained by filtration raw red polymer solution, evaporating solvent under reduced pressure, then pump residual solvent with oil pump.Yellow is obtained without fixed
Type powder 4.92g, yield 93%.Iron content is 26.2%；GPC:Mn=4851g/mol；FT-IR (KBr, main peaks): ν
(cm-1) 3089,2926,2853,1629,1458,1411,1397,1338,1106,1068,1041,1023,999,915,884,
814,482,438；1H NMR (300MHz, CDCl3) δ 4.65~3.36 (m, Cp), 2.71~0.72 (m, CH-CH2)；13C NMR
(101MHz, CDCl3) δ 67.66 (Cp), 43.27 (CH-CH2), 31.86 (CH-CH2), 22.77 (CH3-CH2), 14.34 (CH3-
CH2)。
[embodiment 2]
The amount of n-butyllithium solution in embodiment 1 is only changed to (5mL, 2.5M, 12.5mmol), other operations and embodiment
1 is consistent.Obtain Yellow amorphous powder 5.25g, yield 100%.Iron content is 24.4%；GPC:Mn=442g/mol.FT-IR
(KBr, main peaks): ν (cm-1) 3089,2925,2852,1632,1458,1411,1338,1106,1054,1037,
1023,1000,915,815,483；1H NMR (300MHz, CDCl3) δ 4.65~3.90 (m, Cp), 3.25~0.75 (m, CH-
CH2)；13C NMR (101MHz, CDCl3) δ 67.66 (Cp), 43.27 (CH-CH2), 31.86 (CH-CH2), 22.77 (CH3-CH2),
14.34(CH3-CH2)。
[embodiment 3]
The amount of n-butyllithium solution in embodiment 1 is only changed to (2.5mL, 2.5M, 6.25mmol), other operations and implementation
Example 1 is consistent.Obtain Yellow amorphous powder 5.24g, yield 100%.Iron content is 25.7%；GPC:Mn=724g/mol.FT-
IR (KBr, main peaks): ν (cm-1) 3090,2924,2853,1630,1458,1410,1338,1106,1041,1023,
999,814,482；1H NMR (300MHz, CDCl3) δ 4.80~3.85 (m, Cp), 3.25~0.80 (m, CH-CH2)；13C NMR
(101MHz, CDCl3) δ 67.66 (Cp), 43.27 (CH-CH2), 31.86 (CH-CH2), 22.77 (CH3-CH2), 14.34 (CH3-
CH2)。
[embodiment 4]
The amount of n-butyllithium solution in embodiment 1 is only changed to (2mL, 2.5M, 5mmol), other operations and embodiment 1 one
It causes.Obtain Yellow amorphous powder 5.25g, yield 100%.Iron content is 25.8%；GPC:Mn=799g/mol.FT-IR
(KBr, main peaks): ν (cm-1) 3089,2924,2854,1636,1459,1411,1339,1106,1041,1023,
1000,483；1H NMR (300MHz, CDCl3) δ 4.73~3.60 (m, Cp), 2.77~0.62 (m, CH-CH2)；13C NMR
(101MHz, CDCl3) δ 67.66 (Cp), 43.27 (CH-CH2), 31.86 (CH-CH2), 22.77 (CH3-CH2), 14.34 (CH3-
CH2)。
[embodiment 5]
The amount of n-butyllithium solution in embodiment 1 is only changed to (1.67mL, 2.5M, 4.17mmol), other operations and reality
It is consistent to apply example 1.Obtain Yellow amorphous powder 5.25g, yield 100%.Iron content is 25.8%；GPC:Mn=863g/mol.
FT-IR (KBr, main peaks): ν (cm-1) 3090,2925,2853,1635,1458,1411,1339,1106,1048,
1041,1023,1000,483；1H NMR (300MHz, CDCl3) δ 4.85~3.96 (m, Cp), 3.24~0.73 (m, CH-CH2)
；13C NMR (101MHz, CDCl3) δ 67.66 (Cp), 43.27 (CH-CH2), 31.86 (CH-CH2), 22.77 (CH3-CH2),
14.34(CH3-CH2)。
[embodiment 6]
The amount of n-butyllithium solution in embodiment 1 is only changed to (1.25mL, 2.5M, 3.12mmol), other operations and reality
It is consistent to apply example 1.Obtain Yellow amorphous powder 5.25g, yield 100%.Iron content is 26.4%；GPC:Mn=874g/mol.
FT-IR (KBr, main peaks): ν (cm-1) 3090,2926,2853,1628,1458,1411,1339,1106,1041,
1023,1000,814,483；1H NMR (300MHz, CDCl3) δ 4.88~3.92 (m, Cp), 3.34~0.88 (m, CH-CH2)；13C NMR (101MHz, CDCl3) δ 67.66 (Cp), 43.27 (CH-CH2), 31.86 (CH-CH2), 22.77 (CH3-CH2),
14.34(CH3-CH2)。
[embodiment 7]
The amount of n-butyllithium solution in embodiment 1 is only changed to (1mL, 2.5M, 2.5mmol), other operations and embodiment 1
Unanimously.Obtain Yellow amorphous powder 5.24g, yield 100%.Iron content is 26.3%；GPC:Mn=1107g/mol.FT-IR
(KBr, main peaks): ν (cm-1) 3090,2925,2854,2252,1685,1636,1458,1411,1339,1228,
1106,1041,1023,1000,815,483；1H NMR (300MHz, CDCl3) δ 4.67~3.54 (m, Cp), 2.73~0.69
(m, CH-CH2)；13C NMR (101MHz, CDCl3) δ 67.66 (Cp), 43.27 (CH-CH2), 31.86 (CH-CH2), 22.77
(CH3-CH2), 14.34 (CH3-CH2)。
[embodiment 8]
The amount of n-butyllithium solution in embodiment 1 is only changed to (0.67mL, 2.5M, 1.67mmol), other operations and reality
It is consistent to apply example 1.Obtain Yellow amorphous powder 5.16g, yield 100%.Iron content is 26.2%；GPC:Mn=2143g/mol.
FT-IR (KBr, main peaks): ν (cm-1) 3090,2925,2252,1637,1458,1411,1339,1106,1000,884,
483；1H NMR (300MHz, CDCl3) δ 4.72~3.57 (m, Cp), 2.74~0.53 (m, CH-CH2)；13C NMR (101MHz,
CDCl3) δ 67.66 (Cp), 43.27 (CH-CH2), 31.86 (CH-CH2), 22.77 (CH3-CH2), 14.34 (CH3-CH2)。
[embodiment 9]
The amount of n-butyllithium solution in embodiment 1 is only changed to (0.5mL, 2.5M, 1.25mmol), other operations and implementation
Example 1 is consistent.Obtain Yellow amorphous powder 5.28g, yield 100%.Iron content is 26.2%；GPC:Mn=2972g/mol.
FT-IR (KBr, main peaks): ν (cm-1) 3098,2924,2853,1630,1458,1411,1339,1106,1041,
1023,1000,815,483；1H NMR (300MHz, CDCl3) δ 4.78~3.52 (m, Cp), 2.86~0.52 (m, CH-CH2)；13C NMR (101MHz, CDCl3) δ 67.66 (Cp), 43.27 (CH-CH2), 31.86 (CH-CH2), 22.77 (CH3-CH2),
14.34(CH3-CH2)。
The volatility of vinyl ferrocene oligomer
[embodiment 10]
With gravitational thermal analysis method, the thermochemical property of vinyl ferrocene oligomer prepared by embodiment 1 is analyzed.
[embodiment 11]
With gravitational thermal analysis method, the thermochemical property of vinyl ferrocene oligomer prepared by embodiment 4 is analyzed.
[embodiment 12]
With gravitational thermal analysis method, the thermochemical property of vinyl ferrocene oligomer prepared by embodiment 7 is analyzed.
[embodiment 13]
With gravitational thermal analysis method, the thermochemical property of vinyl ferrocene oligomer prepared by embodiment 8 is analyzed.
[embodiment 14]
With gravitational thermal analysis method, the thermochemical property of vinyl ferrocene oligomer prepared by embodiment 9 is analyzed.
Fig. 1 embodiment Isosorbide-5-Nitrae, the vinyl ferrocene oligomer of 7,8,9 preparations is before 350 DEG C without apparent thermal weight loss
Phenomenon illustrates that this polymer is not volatile before it is decomposed, will not generate ferrocene as small molecule ferrocene derivatives
Steam.
Catalyticing decomposition action of the vinyl ferrocene oligomer to ammonium perchlorate
[embodiment 15]
With differential scanning calorimetric analysis method to pure thin and tall ammonium chlorate (D50=45 μm) thermal decomposition temperature analyzed.
The high-temperature decomposition temperature of the pure thin and tall ammonium chlorate of Fig. 1 is 380 DEG C.
[embodiment 16]
Vinyl ferrocene oligomer dissolution prepared by experimental example 1 in methylene chloride, then by thin and tall ammonium chlorate (D50=
45 μm) polymer solution is added, the mass ratio of vinyl ferrocene oligomer and ammonium perchlorate is 5:95, after mixing vacuum
Solvent is removed, obtains binary mixture, and analyzed with thermal decomposition temperature of the differential scanning calorimetric analysis method to mixture.
Fig. 2 surveys experiment number Ju after the vinyl ferrocene oligomer by adding 5% mass fraction in ammonium perchlorate
Show after adding vinyl ferrocene oligomer, vinyl ferrocene oligomer/thin and tall ammonium chlorate binary mixture high temperature point
It solves temperature and advances to 352 DEG C by 380 DEG C.It can be seen that vinyl ferrocene oligomer has significantly the thermal decomposition of ammonium perchlorate
Catalytic effect.Vinyl ferrocene oligomer/thin and tall ammonium chlorate binary mixture impact sensitivity test
[embodiment 17]
Referring to GJB 772A-97, method 601.1 is to 1 gained vinyl ferrocene oligomer of embodiment/thin and tall ammonium chlorate
(D50=45 μm) binary mixture carries out impact sensitivity test, and 2kg drops hammer, 15cm drop height.Every group of 50 samples, each sample
20mg.Impact sensitivity result is 10%.
[embodiment 18]
As described in Example 17, to 4 gained vinyl ferrocene oligomer of embodiment/thin and tall ammonium chlorate (D50=45 μm)
Binary mixture carries out impact sensitivity test.Impact sensitivity result is 14%.
[embodiment 19]
As described in Example 17, to 8 gained vinyl ferrocene oligomer of embodiment/thin and tall ammonium chlorate (D50=45 μm)
Binary mixture carries out impact sensitivity test.Impact sensitivity result is 14%.
Claims (7)
1. a kind of for being catalyzed the vinyl ferrocene oligomer catalyst of ammonium perchlorate decomposition, vinyl two described in feature
The iron content of luxuriant iron oligomer catalyst is 20.6%~26.3%, and molecular weight is 400~5000；
And the vinyl ferrocene oligomer catalyst has the following structure formula:
Wherein R is normal-butyl or sec-butyl, n=1~24；
And the vinyl ferrocene oligomer catalyst is made by the steps: under the conditions of anhydrous and oxygen-free, in-
At 20~-10 DEG C, tetramethylethylenediamine and butyl lithium solution are added into the THF solution of vinyl ferrocene, reacts 2~8h；
The molar ratio of the vinyl ferrocene and butyl lithium is 1:2~30.
2. vinyl ferrocene oligomer catalyst according to claim 1, it is characterised in that n=2~24.
3. a kind of preparation method of vinyl ferrocene oligomer catalyst according to claim 1, it is characterised in that packet
It includes following steps: under the conditions of anhydrous and oxygen-free, at -20~-10 DEG C, tetramethyl is added into the THF solution of vinyl ferrocene
Base ethylenediamine and butyl lithium solution react 2~8h；The molar ratio of the vinyl ferrocene and butyl lithium is 1:2~30.
4. the preparation method of vinyl ferrocene oligomer catalyst according to claim 3, it is characterised in that gained is anti-
It answers product by purification process: being precipitated and precipitated with organic solvent, filter, washing, then with another kind organic solution dissolving filter cake, mistake
Filter, filtrate steaming removal solvent are purified.
5. the preparation method of vinyl ferrocene oligomer catalyst according to claim 4, it is characterised in that described
Organic solvent for precipitating to be precipitated is methanol, ethyl alcohol, isopropanol or their mixed solvent.
6. the preparation method of vinyl ferrocene oligomer catalyst according to claim 4, it is characterised in that described
Organic solvent for dissolving filter cake is methylene chloride, ethyl acetate, chloroform, 1,2- dichloroethanes or their mixed solvent.
7. a kind of vinyl ferrocene oligomer catalyst according to claim 1 or 2, which is characterized in that the second
Alkenyl ferrocene oligomer catalyst is for being catalyzed in the solid propellant and gas generator propellant using ammonium perchlorate as oxidant
Decompose the catalyst of ammonium perchlorate.
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